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    Reactions and Mechanisms

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    (1) Which member of each pair of reactions occurs the most rapidly and by what mechanisms?

    a. i. (CH3)3CCH2Cl -- CN-, ethanol -->
    ii. PhCH2Cl -- CN-, ethanol -->

    b. i. CH3CH2CH2CH2Br -- CN-, (CH3)2N)2PO -->
    ii. CH3CH2CH2CH2Br -- CN-, CH3OH -->

    c. i. (CH3)3COH -- H30+, 25 degrees Celsius -->
    ii. CH3CH2CH2CH2OH -- H30+, 25 degrees Celsius -->

    (2) When (2S, 3S)-3-bromo-2-methoxybutane undergoes an SN2 reation with methoxide ion then the obtained product is not optically active. Why does the 3-bromo-2-methoxybutane have the formula CH3-CH(OCH3)-CHBr-CH3? Explain.

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    Solution Preview

    2. a) ii will occur most rapidly by SN1 mechanism. In ethanol solvent, both (CH3)3CCH2Cl and PhCH2Cl undergo ionization to yield 1o and benzyl cations, respectively.

    According to the Hammond postulate, the first transition state in an SN1 reaction will have a structure ...

    Solution Summary

    The expert examines reaction mechanisms.